Certain substituted 3-amino-2-benzoylcyclohex-2-enones

ABSTRACT

A compound of the formula ##STR1## wherein R is halogen, C 1  -C 2  alkyl, C 1  -C 2  alkoxy, nitro; cyano; C 1  -C 2  haloalkyl, or R a  SO n  - wherein n is 0 or 2 and R a  is C 1  -C 2  alkyl; R 1  is hydrogen or C 1  -C 4  alkyl; R 2  is hydrogen or C 1  -C 4  alkyl; or R 1  and R 2  together are alkylene having 2 to 5 carbon atoms; R 3  is hydrogen or C 1  -C 4  alkyl; R 4  is hydrogen or C 1  -C 4  alkyl; or C 3  and R 4  are oxo; R 5  is hydrogen or C 1  -C 4  alkyl; R 6  is hydrogen or C 1  -C 4  alkyl; and R 7  and R 8  independently are (1) hydrogen; (2) halogen; (3) C 1  -C 4  alkyl; (4) C 1  -C 4  alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C 1  -C 4  haloalkyl; (9) R b  SO n  - wherein n is the integer 0, 1 or 2; and R b  is (a) C 1  -C 4  alkyl; (b) C 1  -C 4  alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR c  R d  wherein R c  and R d  independently are hydrogen or C 1  -C 4  alkyl; (11) R e  C(O)--wherein R e  is C 1  -C 4  alkyl or C 1  -C 4  alkogxy; (12) SO 2  NR c  R d  wherein R c  and R d  are as defined; or (13) --N(R c )C(O)R d  wherein R c  and R d  are as defined; R 9  is hydrogen or C 1  -C 4  alkyl, R 10  is (a) hydrogen; (b) C 1  -C 6  alkyl, (c) C 4  -C 6  cycloalkyl, (d) substituted C 1  -C 6  alkyl, (e) phenyl; (f) substituted phenyl; (g) C 1  -C 6  alkoxy; (h) benzyl; (i) phenethyl; (j) C 1  -C 4  alkyl-C(O)-; (k) C 1  -C 4  alkyoxy-C(O)-; (1) C 2  -C 6  alkenyl; or (m) C 2  -C 6  alkynyl; and R 9  and R 10  together form a heterocyclic ring with the nitrogen to which they are attached containing 0, 1 or 2 additional hetero atoms (nitrogen, sulfur or oxygen).

BACKGROUND OF THE INVENTION

Compounds having the structural formula ##STR2## wherein R₁ and R₂ are hydrogen or alkyl are described in Chem. Pharm. Bull., 30(5), 1692-1696 (1982). No utility is taught for the compounds.

DESCRIPTION OF THE INVENTION

This invention relates to 3-amino-2-benzoylcyclohex-2-enones and their use as herbicides.

One embodiment of this invention is an herbicidal composition comprising an herbicidally active substituted 3-amino-2-benzoylcyclohex-2-enones and an inert carrier therefor wherein the 2-position of the benzoyl moiety is substituted as herein recited and the 4-position preferably is substituted with an electron withdrawing group, such as halogen, cyano, trifluoromethyl or nitro. The 4-, 5- and 6-positions of the cyclohex-2-enone moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the cyclohex-2-enone moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

Also embodied within the scope of this invention are novel compounds having the following structural formula ##STR3## wherein

R is halogen; C₁ -C₂ alkyl, preferably methyl; C₁ -C₂ alkoxy, preferably methoxy; nitro; cyano; C₁ -C₂ haloalkyl, preferably trifluoromethyl; or R^(a) SO_(n) -- wherein n is 0 or 2, preferably 2 and R^(a) is C₁ -C₂ alkyl, preferably methyl. Preferably, R is chlorine, bromine, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, cyano, nitro, C₁ -C₂ alkylthio or C₁ -C₂ alkylsulfonyl; more preferably chlorine, nitro, methyl, trifluoromethyl or methylsulfonyl;

R¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R¹ is hydrogen or methyl;

R² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R² is hydrogen or methyl; or

R¹ and R₂ together are alkylene having 2 to 5 carbon atoms;

R³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³ is hydrogen or methyl;

R⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴ is hydrogen or methyl; or

R³ and R⁴ together are oxo;

R⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵ is hydrogen or methyl;

R⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁶ is hydrogen; or

R⁵ and R⁶ together are alkylene having 2 to 5 carbon atoms;

R⁷ and R⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl;

(11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy;

(12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined;

(13) --N(R^(c))C(O)R^(d) wherein R^(c) and R^(d) are as defined; and

R⁹ is hydrogen or C₁ -C₄ alkyl, preferably methyl or ethyl;

R¹⁰ is

(a) hydrogen;

(b) C₁ -C₆ alkyl, preferably C₁ -C₂ alkyl;

(c) C₄ -C₆ cycloalkyl;

(d) substituted C₁ -C₆ alkyl, preferably C₁ -C₄ alkyl wherein the substitutions are halogen, hydrogen, cyano, or carboxy;

(e) phenyl;

(f) substituted phenyl;

(g) C₁ -C₆ alkoxy, preferably C₁ -C₄ alkoxy;

(h) benzyl;

(i) phenethyl;

(j) C₁ -C₄ alkyl-C(O)-;

(k) C₁ -C₄ alkoxy-C(O)-;

(l) C₂ -C₆ alkenyl, preferably C₃ -C₄ alkenyl; or more preferably allyl and methallyl; or

(m) C₂ -C₆ alkynyl; or

R⁹ and R¹⁰ together form a heterocyclic ring with the nitrogen to which they are attached containing 0, 1 or 2 additional hetero atoms (nitrogen, sulfur or oxygen).

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The term "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "C₁ -C₄ haloalkyl" includes the alkyl groups defined above under C₁ -C₄ alkyl in which one or more hydrogen is replaced by chloro, bromo, iodo or fluoro.

Preferably R⁷ is in the 3-position. More preferably R⁷ is hydrogen, chorine, fluorine, trifluoromethyl, cyano, C₁ -C₄ alkoxy, or C₁ -C₄ thioalkyl. More preferably, R⁷ is hydrogen. Preferably R⁸ is in the 4-position. Most preferably R⁸ is halogen, cyano, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl or C₁ -C₄ haloalkyl, preferably chloromethyl, difluoromethyl or trifluoromethyl.

The compounds of this invention are active herbicides of a general type. That is, they are herbicidally effective against a wide range of plant species. The method of controlling undesirable vegetation of the present invention comprises applying an herbicidally effective amount of the above-described compounds to the area where control is desired.

The compounds of the present invention can be prepared by the following two-step general method. ##STR4## wherein R through R⁸ are as defined.

Generally in step (a) the benzoyl dione is dissolved in an inert solvent such as methylene dichloride and an excess, usually 150 to 200 mole percent, of oxalyl chloride is added followed by a catalytic amount (0.1 equivalent) of dimethylformamide. The reaction mixture is stirred from one hour to one day at room temperature. The reaction product is isolated using conventional techniques. ##STR5## wherein R through R¹⁰ are as defined.

Generally, in step (b) the 3-chloro-2-benzoylcycloalk-2-enone is reacted with 200 to 250 mole percent of primary or secondary amine in an inert solvent. The mixture is stirred 1 to 18 hours and the product is isolated using conventional techniques.

The precursor benzoyl diones used in step (a) can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR6## wherein R through R⁸ are as defined and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably is added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete.

The reaction product is worked up by conventional techniques. ##STR7## wherein R through R⁸ are as defined.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the moderate base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably about 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 80° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents are useful in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which can be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangement may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR8## wherein R, R⁷ and R⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are four representative examples of the methods described therein. ##STR9## wherein R, R⁷ and R⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR10## wherein R, R⁷ and R⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR11## wherein R, R⁷ and R⁸ are as defined and X is chlorine, bromine or iodine.

The substituted aromatic halide is allowed to react with magnesium in a solvent such as ether. The solution is then poured over crushed dry ice and the benzoic acid is isolated by conventional techniques.

The following examples teach the synthesis of a representative compound of this invention.

EXAMPLE I 2-(2-Chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione ##STR12##

1,3-Cyclohexanedione [11.2 grams (g), 0.1 mole] and 23.3 g (0.1 mole) 2-chloro-4-methanesulfonylbenzoyl chloride were dissolved in 200 ml methylene chloride at room temperature. Triethylamine (11 g, 0.11 mole) was slowly added with cooling. The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase dried with MgSO₄ and then evaporated to yield the intermediate enol ester 3-(2-chloro-4-methanesulfonylbenzoyloxy)cyclohex-2-enone. The 3-(2-chloro-4-methanesulfonylbenzoyloxy)cyclohex-2-enone was dissolved in 200 ml acetonitrile and triethylamine (22 g, 0.22 mole) was added all at once, followed by acetonecyanohydrin (0.8 g, 0.01 mole). The solution was stirred for 5 hours and then poured into 2N HCl and extracted twice with ethyl acetate. The organic layer was dried with MgSO₄ and the solventevaporated to yield the product.

EXAMPLE II 3-Chloro-2-(2-chloro-4-methanesulfonylbenzoyl)cyclohex-2-enone ##STR13##

2-(2-Chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione [9.8 g, 30 millimole (mmol)] was dissolved in 100 ml methylene chloride and stirred at room temperature. To this solution was added oxalyl chloride (5.7 g, 45mmol) followed by dimethylformamide (0.5 ml) in portions small enough to control effervescence. The resulting solution was stirred for 4 hours and then poured into water and extracted with methylene chloride. The organic layer was washed again with water, saturated K₂ CO₃ solution andthen dried with MgSO₄ and the solvent evaporated to yield 3-chloro-2(2-chloro-4-methanesulfonylbenzoyl)cyclohex-2-enone (7.3 g, 70%)as an oil which was used without further purification.

EXAMPLE III 2-(2-Chloro-4-methanesulfonylbenzoyl)-3-N-methyl, N-methoxyamino-cyclohex-2-enone ##STR14##

3-Chloro-2-(2-chloro-4-methanesulfonylbenzoyl)-cyclohex-2-enone (8.0 g, 23 millimole) was dissolved in 80 ml THF and stirred at room temperature. N,O-Dimethylhydroxylamine hydrochloride (2.5 g, 27 millimole) and triethylamine (4.6 g, 46 millimole) were added all at once, and the reaction mixture stirred for 4 hours. The reaction mixture was then pouredinto 1N HCl solution and extracted with ethyl acetate. The organic layer was washed with 5% K₂ CO₃, dried with MgSO₄ and the solventevaporated to yield a solid: 2.2 g, 27%, m.p. 109°-112° C. The structure is consistent with nuclear magnetic resonance, infrared and mass spectral data.

The following is a table of certain selected compounds that are preparable according to the procedure described herein. Compound numbers are assignedto each compound and are used throughout the remainder of the application.

                                      TABLE I                                      __________________________________________________________________________      ##STR15##                                                                     Comp.                                                                          No. R  R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                           R.sup.4                                                                           R.sup.5                                                                           R.sup.6                                                                           R.sup.7                                                                          R.sup.8 R.sup.9                                                                             R.sup.10                               __________________________________________________________________________      1  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            OCH.sub.3                               2  Cl H  H  H  H  H  H  H 4-Cl    H    OC.sub.2 H.sub.5                        3  Cl H  H  H  H  H  H  H 4-NO.sub.2                                                                             CH.sub.3                                                                            OCH.sub.3                               4  Cl H  H  H  H  H  H  H 4-Cl    H    OCH.sub.3                               5  Cl H  H  CH.sub. 3                                                                         CH.sub.3                                                                          H  H  H 4-NO.sub.2                                                                             CH.sub.3                                                                            OCH.sub.3                               6  Cl H  H  H  H  H  H  H 4-NO.sub.2                                                                             CH.sub.3                                                                            OCH.sub.3                               7  Cl H  H  CH.sub.3                                                                          CH.sub.3                                                                          H  H  H 4-SO.sub.2i-C.sub.3 H.sub.7                                                            CH.sub.3                                                                            OCH.sub.3                               8  Cl H  H  H  H  H  H  H 4-SO.sub.2i-C.sub.3 H.sub.7                                                            CH.sub.3                                                                            OCH.sub.3                               9  Cl H  H  H  H  H  H  H 4-SO.sub.2n-C.sub.4 H.sub.9                                                            CH.sub.3                                                                            OCH.sub.3                              10  NO.sub.2                                                                          H  H  CH.sub.3                                                                          CH.sub.3                                                                          H  H  H 4-Cl    CH.sub.3                                                                            OCH.sub.3                              11  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H 4-Cl    CH.sub.3                                                                            OCH.sub.3                              12  CH.sub.3                                                                          H  H  H  H  H  H  H H       CH.sub.3                                                                            OCH.sub.3                              13  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            CH.sub.3                               14  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            H                                      15  Cl H  H  H  H  H  H  H 4-Cl    C.sub.2 H.sub.5                                                                     H                                       16.sup.(a)                                                                        Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            OCH.sub.3                              17  Cl H  H  H  H  H  H  H 4-SO.sub.2C.sub.2 H.sub.5                                                              CH.sub.3                                                                            OCH.sub.3                              18  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H H       CH.sub.3                                                                            OCH.sub.3                              19  Cl H  H  H  H  H  H  Cl                                                                               4-SO.sub.2C.sub.2 H.sub.5                                                              CH.sub.3                                                                            OCH.sub.3                              20  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2        21  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2         22  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.2 SCH.sub.2 CH.sub.2                 23  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            C.sub.2 H.sub.5 OC(O)CH.sub.2          24  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                             ##STR16##                             25  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    H    CH.sub.2C(CH.sub.3)CH.sub.2            26  Cl H  H  H  H  H  H  H 4-Cl    H    CH.sub.2C(CH.sub.3)CH.sub.2            27  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.2 SCH.sub.2 CH.sub.2                 28  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            C.sub.2 H.sub.5 OC(O)CH.sub.2          29  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                             ##STR17##                             30  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            HOCH.sub.2 CH.sub.2                    31  CH.sub.3                                                                          H  H  H  H  H  H  H 4-Br    CH.sub.3                                                                            OCH.sub.3                              32  Cl H  H  H  H  H  H  Cl                                                                               4-Cl    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2         33  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H H       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2         34  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H H       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2        35  Cl H  H  H  H  H  H  Cl                                                                               4-Cl    CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2        36  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            HOCH.sub.2 CH.sub.2                    37  Cl H  H  H  H  H  H  H 4-Cl    H    H                                      38  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H 4-CF.sub.3                                                                             C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        39  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H 4-SO.sub.2 C.sub.2 H.sub.5                                                             C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        40  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            phenyl                                 41  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            phenyl                                 42  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            benzyl                                 43  Cl H  H  H  H  H  H  H 4-Cl    H    phenyl                                 44  Cl H  H  H  H  H  H  H 4-Cl    Et   (CH.sub.3).sub.2 CHCH(CH.sub.3)        45  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            cyclopentyl                            46  Cl H  H  H  H  H  H  H 4-Cl    H    CH.sub.2 CN                            47  NO.sub.2                                                                          H  H  H  H  H  H  H 4-CF.sub.3                                                                             C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        48  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            benzyl                                 49  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    C.sub.2 H.sub.5                                                                     (CH.sub.3).sub.2 CHCH(CH.sub.3)        50  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            cyclopentyl                            51  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            HCCCH.sub.2                            52  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            NCCH.sub.2 CH.sub.2                    53  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            NCCH.sub.2 CH.sub.2                    54  Cl H  H  H  H  H  H  H 4-Cl                                                                                    ##STR18##                                  55  Cl H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                             ##STR19##                             56  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                             ##STR20##                             57  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H 4-Cl    C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        58  Cl H  H  H  H  H  H  H 4-Cl    H    HOCH.sub.2 CH.sub.2                    59  NO.sub.2                                                                          H  H  H  H  H  H  H 4-Cl    C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        60  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H 4-Br    C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        61  NO.sub.2                                                                          H  H  H  H  H  H  H 4-Cl    CH.sub.3                                                                            OCH.sub.3                              62  NO.sub.2                                                                          H  H  H  H  H  H  H H       CH.sub.3                                                                            OCH.sub.3                              63  Cl H  H  H  H  H  H  H 4-Cl    C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        64  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H H       CH.sub.3                                                                            CH.sub.3                               65  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H H       CH.sub.3                                                                            H                                      66  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H H       C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        67  Cl H  H  H  H  H  H  H 4-SO.sub.2 CH.sub.3                                                                    C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        68  Cl CH.sub.3                                                                          CH.sub.3                                                                          oxo   CH.sub.3                                                                          CH.sub.3                                                                          H 4-CH.sub.3 SO.sub.2                                                                    CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2        69  NO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3                                                                          oxo   CH.sub.3                                                                          CH.sub.3                                                                          H H       C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        70  H  CH.sub.3                                                                          CH.sub.3                                                                          oxo   CH.sub.3                                                                          CH.sub.3                                                                          H H       CH.sub.3                                                                             ##STR21##                             71  H  CH.sub.3                                                                          CH.sub.3                                                                          oxo   CH.sub.3                                                                          CH.sub.3                                                                          H 4-Cl    C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                        __________________________________________________________________________      .sup.(a) Prepared in Example III.                                        

Herbicidal Screening Tests

As previously mentioned, the herein described compounds produced in the above-described manner are phytotoxic compounds which are useful and valuable in controlling various plant species. Selected compounds of this invention were tested as herbicides in the following manner.

Pre-emergence herbicide test. On the day preceding treatment, seeds of seven different weed species are planted in loamy sand soil in individual rows using one species per row across the width of a flat. The weeds used are green foxtail (FT) (Setaria viridis), watergrass (WG) (Echinochloa crusgalli), wild oat (WO) (Avena fatua), annual morningglory (AMG) (Ipomoea lacunosa), velvetleaf (VL) (Abutilon theophrasti), Indian mustard(MD) (Brassica juncea) and yellow nutsedge (YNS) (Cyperus esculentus). Ample seeds are planted to give about 20 to 40 seedlings per row, after emergence, depending upon the size of the plants.

Using an analytical balance, 600 milligrams (mg) of the compound to be tested are weighed out on a piece of glassine weighing paper. The paper and compound are placed in a 60 milliliter (ml) wide-mouth clear bottle and dissolved in 45 ml of acetone or substituted solvent. Eighteen ml of this solution are transferred to a 60 ml wide-mouth clear bottle and diluted with 22 ml of a water and acetone mixture (19:1) containing enoughpolyoxyethylene sorbitan monolaurate emulsifier to give a final solution of0.5% (v/v). The solution is then sprayed on a seeded flat on a linear spraytable calibrated to deliver 80 gallons per acre (748 L/ha). The applicationrate is 4 lb/acre (4.48 Kg/ha).

After treatment, the flats are placed in the greenhouse at a temperature of70° to 80° F. and watered by sprinkling. Two weeks after treatment, the degree of injury or control is determined by comparison with untreated check plants of the same age. The injury rating from 0 to 100% is recorded for each species as percent control with 0% representing no injury and 100% representing complete control.

The results of the tests are shown in the following Table II.

                  TABLE II                                                         ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.    FT      WG     WO    AMG   VL    MD   YNS                               ______________________________________                                          1     80      90     0     30    100   85   80                                 2     25      35     0     0     50    0    20                                 3     100     75     20    20    100   95   75                                 4     20      20     0     0     25    20   0                                  5     100     100    30    40    100   100  90                                 6     40      100    0     0     100   100  0                                  7     0       25     0     0     50    100  0                                  8     0       30     0     40    90    100  90                                 9     20      90     0     100   100   100  80                                10     100     90     40    100   100   100  90                                11     100     100    70    100   100   100  90                                12     50      0      0     0     0     0    0                                 13     0       100    0     5     100   95   70                                14     0       90     0     0     100   100  50                                15     0       40     0     0     0     0    40                                16     100     100    100   100   100   100  80                                17     95      100    80    100   100   100  80                                18     100     100    90    50    100   100  80                                19     100     100    30    100   100   100  80                                20     100     100    80    100   100   100  80                                21     0       65     0     25    100   90   80                                22     100     100    50    100   100   100  80                                23     100     100    80    100   100   100  80                                24     100     100    80    100   100   100  80                                25     0       0      0     0     100   50   80                                26     10      40     0     0     100   95   80                                27     100     100    40    100   100   100  80                                28     100     100    20    50    100   100  80                                29     100     100    50    100   100   100  80                                30     100     100    50    90    100   100  80                                31     5       70     0     20    100   100  80                                32     5       40     10    0     100   85   60                                33     5       50     10    0     0     0    20                                34     100     100    95    75    100   100  80                                35     100     100    10    75    100   100  80                                36     100     100    90    100   100   100  80                                37     0       100    0     10    100   100  80                                38     100     100    85    100   100   100  80                                39     100     100    80    100   100   100  80                                40     0       80     0     5     90    90   70                                41     100     100    80    100   100   100  80                                42     95      98     10    100   100   100  80                                43     0       0      0     5     10    20   0                                 44     5       85     0     0     100   100  80                                45     30      85     0     10    100   100  80                                46     100     100    10    100   100   100  80                                47     100     100    80    100   100   100  80                                48     100     100    30    100   100   100  80                                49     10      100    0     100   100   100  80                                50     100     100    10    100   100   100  80                                51     100     100    80    80    100   100  80                                52     100     100    10    100   100   100  80                                53     100     100    80    100   100   100  --                                54     100     100    30    100   100   100  80                                55     100     100    5     80    100   100  80                                56     100     100    30    100   100   100  80                                57     100     100    80    100   100   100  80                                58     0       20     0     0     100   90   80                                59     100     100    70    70    100   100  80                                60     100     100    0     5     100   100  80                                68     100     100    100   100   100   100  80                                69     100     100    100   100   100   100  80                                70     100     100    95    100   100   100  80                                71     100     100    100   100   100   100  80                                ______________________________________                                         (--) = Not tested.                                                        

Post-emergence Herbicide Test: This test is conducted in an identical manner to the testing procedure for the pre-emergence herbicide test, except the seeds of the seven different weed species are planted 10-12 days before treatment. Also, watering of the treated flats is confined to the soil surface and not to the foilage of the sprouted plants.

The results of the post-emergence herbicide test are reported in Table III.

                  TABLE III                                                        ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.    FT      WG     WO    AMG   VL    MD   YNS                               ______________________________________                                          1     80      100    20    100   100   100  50                                 2     65      50     0     40    75    75   15                                 3     50      60     10    50    100   100  60                                 4     0       20     10    25    50    40   0                                  5     90      70     50    40    80    80   60                                 6     20      60     0     35    100   100  30                                 7     10      60     0     50    50    90   0                                  8     50      40     20    50    100   100  80                                 9     0       100    0     100   100   100  80                                10     90      100    30    50    65    70   65                                11     100     100    70    100   100   100  80                                12     10      0      0     10    40    10   0                                 13     0       10     65    95    100   95   30                                14     0       20     0     90    95    80   30                                15     0       20     0     90    95    80   10                                16     100     95     100   90    100   100  80                                17     85      100    65    90    90    100  80                                18     85      65     90    40    85    80   80                                19     100     100    80    90    90    100  80                                20     100     100    100   100   100   100  70                                21     80      100    0     100   95    100  --                                22     100     100    98    100   98    100  80                                23     100     100    100   100   100   100  80                                24     100     100    95    100   100   100  80                                25     0       10     0     10    50    20   10                                26     0       20     0     10    50    20   0                                 27     100     100    90    100   100   100  70                                28     100     100    85    100   100   100  80                                29     90      100    50    100   100   100  70                                30     100     95     50    100   100   100  70                                31     80      70     0     70    100   100  0                                 32     30      60     0     10    50    80   30                                33     30      50     40    20    50    10   30                                34     100     85     85    90    90    90   80                                35     90      90     50    100   100   100  80                                36     100     95     90    85    98    100  80                                37     0       50     0     30    80    50   30                                38     100     90     100   95    80    100  80                                39     100     100    100   90    100   100  30                                40     10      75     0     25    100   100  0                                 41     100     100    100   100   100   100  --                                42     30      100    20    100   100   100  0                                 43     0       0      0     5     0     0    0                                 44     10      90     0     80    100   100  30                                45     80      100    0     100   100   100  30                                46     100     100    85    100   100   100  --                                47     100     100    100   100   100   100  70                                48     60      80     50    50    80    80   30                                49     10      80     30    50    80    80   30                                50     50      80     30    50    80    90   70                                51     100     100    80    80    100   100  80                                52     100     100    10    100   100   100  80                                53     100     100    80    100   100   100  --                                54     100     100    30    100   100   100  80                                55     100     100    5     80    100   100  80                                56     95      90     80    100   100   100  80                                57     85      80     80    50    85    90   40                                58     10      30     20    10    90    50   20                                59     80      80     80    90    90    100  80                                60     80      80     50    50    90    100  80                                68     85      80     85    60    80    80   70                                69     80      80     80    80    80    80   80                                70     60      70     50    80    90    90   60                                71     100     100    100   100   100   100  80                                ______________________________________                                         (--)  Not tested.                                                         

Pre-Emergence Multi-Weed Herbicide Test

Several compounds were evaluated at an application rate of 1/2 lb/acre (0.56 kg/ha) for pre-emergence activity against a larger number of weed species.

Pre-Emergence Multi-Weed Herbicide Test

Several compounds were evaluated at an application rate of 1/2 lb/acre (0.56 kg/ha) for pre-emergence activity against a larger number of weed species.

The process was generally similar to the pre-emergence herbicide test described above except that only 150 or 75 milligrams of test compound were weighed out and the application rate was 40 gallons per acre.

Redroot pigweed (PW) and curly dock (CD) were eliminated in this test and the following weed species were added:

    ______________________________________                                         Grasses:                                                                       ______________________________________                                         downy brome   Bromus tectorum  (DB)                                            annual ryegrass                                                                              Lolium multiflorum                                                                              (ARG)                                           shattercane   Sorghum bicolor  (SHC)                                           broadleaf signalgrass                                                                        Brachiaria platyphylla                                                                          (BSG)                                           hemp sesbania Sesbania exaltata                                                                               (SESB)                                          sicklepod     Cassia obtusifolia                                                                              (SP)                                            cocklebur     Xanthium sp.     (CB)                                            ______________________________________                                    

The results of the test are shown in Table IV.

                                      TABLE IV                                     __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     61  60 100                                                                               100 100                                                                               85 65 85 25  80  100                                                                               35 100                                                                               95 65                               62  60 100                                                                               75  80 75 20 70 25  90  100                                                                               0  100                                                                               50 50                               63  -- 25 25  100                                                                               30 0  50 25  50  100                                                                               25 -- 0  20                               64  -- 35 30  60 50 20 0  20  50  60 30 -- 35 100                              65  -- 100                                                                               60  80 60 20 0  25  35  50 0  -- 0  0                                66  -- 100                                                                               85  100                                                                               100                                                                               30 35 35  60  75 0  -- 50 100                              67  -- 80 80  100                                                                               85 20 80 95  100 100                                                                               45 -- -- 100                              __________________________________________________________________________     (--)  Not tested.                                                         

Post-Emergence Multi-Weed Herbicide Test: This test is conducted in an identical manner to the testing procedure for the post-emergence herbicidetest, except the seeds of the seven weed species used in the pre-emergence multi-weed herbicide test were used and the seeds were planted 10-12 days before treatment. Also, watering of the treated flats is confined to the soil surface and not to the foliage of the sprouted plants.

The results of the post-emergence multi-weed herbicide test are reported inTable V.

                                      TABLE V                                      __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     61  35 40 60  70 65 20 65 100 100 100                                                                               85 95 60 95                               62  50 100                                                                               75  100                                                                               75 20 85 40  80  90 0  35 20 20                               63  -- 0  0   90 20 0  75 100 100 100                                                                               50 -- 10 50                               64  -- 35 0   60 40 20 20 55  65  100                                                                               0  -- 0  100                              65  -- 40 20  50 50 0  25 50  60  85 0  -- 20 25                               66  -- 100                                                                               35  70 70 0  75 60  75  100                                                                               40 -- 40 100                              67  -- 0  0   100                                                                               0  0  95 98  100 98 45 -- 40 95                               __________________________________________________________________________     (--) = Not Tested.                                                        

The compounds of the present invention are useful as herbicides and can be applied in a variety of ways at various concentrations. In practice, the compounds herein defined are formulated into herbicidal compositions, by admixture, in herbicidally effective amounts, with the adjuvants and carriers normally employed for facilitating the dispersion of active ingredients for agricultural applications, recognizing the fact that the formulation and mode of application of a toxicant may affect the activity of the materials in a given application. Thus, these active herbicidal compounds may be formulated as granules of relatively large particle size,as wettable powders, as emulsifiable concentrates, as powdery dusts, as flowables, as solutions or as any of several other known types of formulations, depending upon the desired mode of application. These formulations may contain as little as about 0.5% to as much as about 95% or more by weight of active ingredient. A herbicidally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application varies from about 0.01 to approximately 10 pounds per acre, preferably from about 0.02 to about 4 pounds per acre.

Wettable powders are in the form of finely divided particles which dispersereadily in water or other dispersants. The wettable powder is ultimately applied to the soil either as a dry dust or as a dispersion in water or other liquid. Typical carriers for wettable powders include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic diluents. Wettable powders normally are prepared to contain about 5% to about 95% of the active ingredient and usually also contain a small amountof wetting, dispersing, or emulsifying agent to facilitate wetting and dispersion.

Emulsifiable concentrates are homogeneous liquid compositions which are dispersible in water or other dispersant, and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthal, isophorone and other non-volatile organic solvents. For herbicidal application, these concentrates are dispersed in water or other liquid carrier and normally applied as a spray to the area to be treated. The percentage by weight of the essential active ingredient may vary accordingto the manner in which the composition is to be applied, but in comprises about 0.5% to 95% of active ingredient by weight of the herbicidal composition.

Granular formulations wherein the toxicant is carried on relatively coarse particles, are usually applied without dilution to the area in which suppression of vegetation is desired. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite and other organic or inorganic materials which absorb or which may be coated with the toxicant.Granular formulations normally are prepared to contain about 5% to about 25% of active ingredients which may include surface-active agents such heavy aromatic naphthas, kerosene or other petroleum fractions, or vegetable oils; and/or stickers such as destrins, glue or synthetic resins.

Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, for example, the alkyl and alkylaryl sulfonates and sulfates and their salts; polyhydric alcohols; polyethoxylated alcohols; esters and fatty amines; and other types of surface-active agents, many ofwhich are available in commerce. The surface-active agent, when used, normally comprises from 0.1% to 15% by weight of the herbicidal composition.

Dusts, which are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers for the toxicant, are useful formulations for soil-incorporating application.

Pastes, which are homogeneous suspensions of a finely divided solid toxicant in a liquid carrier such as water or oil, are employed for specific purposes. These formulations normally contain about 5% to about 95% of active ingredient by weight, and may also contain small amounts of a wetting, dispersing or emulsifying agent to facilitate dispersion. For application, the pastes are normally diluted and applied as a spray to thearea to be affected.

Other useful formulations for herbicidal applications include simple solutions of the active ingredient in a dispersant in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurized sprays, typically aerosols, wherein the active ingredient is dispersed in finely-divided form as a result of vaporization of a low boiling dispersant solvent carrier, such as the Freons, may also be used.

The phytotoxic compositions of this invention can be applied to the plants in the conventional manner. Thus, the dust and liquid compositions can be applied to the plant by the use of power-dusters, boom and hand sprayers and spray dusters. The compositions can also be applied from airplanes as a dust or a spray or by rope wick applications because they are effective in very low dosages. In order to modify or control growth of germinating seeds or emerging seedlings, as a typical example, the dust and liquid compositions can be applied to the soil according to conventional methods and can be distributed in the soil to a depth of at least 1/2 inch below the soil surface. It is not necessary that the phytotoxic compositions be mechanically admixed with the soil particles since these compositions can also be applied merely by spraying or sprinkling the surface of the soil. The phytotoxic compositions of this invention can also be applied by addition to irrigation water supplied to the field to be treated. This method of application permits the penetration of the compositions into thesoil as the water is absorbed therein. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil canbe distributed below the surface of the soil by conventional means such as discing, dragging or mixing operations.

    ______________________________________                                         EMULSIFIABLE CONCENTRATE FORMULATIONS                                          General Formula with Ranges                                                                     Specific Formula                                              ______________________________________                                         Herbicidal compound                                                                         5-55    herbicidal compound                                                                            24                                        surfactant(s)                                                                               5-25    proprietary blend of oil-                                                                      10                                        solvent(s)   20-90   soluble sulfonates and                                                 100%    polyoxyethylene ethers                                                         polar solvent   27                                                             petroleum hydrocarbon                                                                          39                                                                              100%                                     ______________________________________                                    

    ______________________________________                                         WETTABLE POWDER FORMULATIONS                                                   ______________________________________                                         herbicidal compound                                                                          3-90   herbicidal compound                                                                            80                                        wetting agent                                                                               0.5-2   sodium dialkyl  0.5                                       dispersing agent                                                                            1-8     naphthalene sulfonate                                     diluent(s)   8.5-87  sodium lignosulfonate                                                                          7                                                      100%    attapulgite clay                                                                               12.5                                                                           100%                                      ______________________________________                                    

    ______________________________________                                         EXTRUDED GRANULAR FORMULATIONS                                                 ______________________________________                                         herbicidal compound                                                                         1-20    herbicidal compound                                                                            10                                        binding agent                                                                               0-10    lignin sulfonate                                                                                5                                        diluent(s)   70-99   calcium carbonate                                                                              85                                                     100%                     100%                                     ______________________________________                                    

    ______________________________________                                         FLOWABLE FORMULATIONS                                                          ______________________________________                                         herbicidal 20-70     herbicidal compound                                                                            45                                        compound             polyoxyethylene ether                                                                          5                                         surfactant(s)                                                                              1-10     attagel         0.05                                      suspending agent(s)                                                                       0.05-1    propylene glycol                                                                               10                                        antifreeze agent                                                                           1-10     1,2-benzisothiazoline-3-one                                                                    0.03                                      antimicrobial agent                                                                        1-10     silicone defoamer                                                                              0.02                                      antifoam agent                                                                            0.1-1     water           39.9                                      solvent     7.95-77.85               100%                                                 100%                                                                ______________________________________                                    

The phytotoxic compositions of this invention can also contain other additives, for example, fertilizers, other herbicides and other pesticides, used as adjuvant or in combination with any of the above-described adjuvants. Fertilizers useful in combination with the active ingredients include, for example, ammonium nitrate, urea and superphosphate. 

What is claimed is:
 1. A compound of the formula ##STR22## wherein R is halogen, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, nitro; C₁ -C₂ haloalkyl, or R^(a) SO_(n) -- wherein n is 0 or 2 and R^(a) is C₁ -C₂ alkyl;R¹ is hydrogen or C₁ -C₄ alkyl; R² is hydrogen or C₁ -C₄ alkyl; R³ is hydrogen or C₁ -C₄ alkyl; R⁴ is hydrogen or C₁ -C₄ alkyl; R⁵ is hydrogen or C₁ -C₄ alkyl; R⁶ is hydrogen or C₁ -C₄ alkyl; R⁷ and R⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) nitro; (7) C₁ -C₄ haloalkyl; (8) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen; (c) phenyl; or (d) benzyl; or (9) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R⁹ is hydrogen or C₁ -C₄ alkyl, R¹⁰ is (a) hydrogen; (b) C₁ -C₆ alkyl, (c) C₄ -C₆ cycloalkyl, (d) halogen substituted C₁ -C₆ alkyl, (e) phenyl; (f) C₁ -C₆ alkoxy; (g) benzyl; (h) phenethyl; (i) C₂ -C₆ alkenyl; or (j) C₂ -C₆ alkynyl.
 2. The compounds of claim 1 wherein R is chlorine, bromine, C₁ C₂ alkyl, C₁ -C₂ alkoxy, nitro, C₁ -C₂ alkylthio or C₁ -C₂ alkylsulfonyl; R¹ is hydrogen or methyl; R² is hydrogen or methyl; R³ is hydrogen or methy; R⁴ is hydrogen or methy; R⁵ is hydrogen or methyl; R⁶ is hydrogen or methyl; R⁷ and R⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifloromethoxy; (6) nitro; (7) C₁ -C₄ haloalkyl; (8) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen; (c) phenyl; or (d) benzyl; or (9) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; and R⁹ is hydrogen or methyl and R¹⁰ is (a) hydrogen; (b) C₁ -C₂ alkyl; (c) cyclohexyl; (d) C₁ -C₄ alkoxy; (e) phenyl; (f) benzyl; (g) phenethyl; or (h) allyl.
 3. The compounds of claim 2 wherein R⁷ and R⁸ are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; nitro; trifluoromethyl; R^(b) SO_(n) -- wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; and R⁷ is in the 3-position.
 4. The compound of claim 2 wherein R⁷ is hydrogen and R⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 5. The compound of claim 2 wherein R is chlorine; R¹ is hydrogen; R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4-chlorine; R⁹ is methyl; and R¹⁰ is methoxy.
 6. The compound of claim 2 wherein R is nitro; R¹ is hydrogen; R² is hydrogen; R³ is methyl; R⁴ is methyl; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4-chlorine; R⁹ is methyl; and R¹⁰ is methoxy.
 7. The compound of claim 2 wherein R is methyl; R¹ is methyl; R² is methyl; R³ is hydrogen; R⁴ is hydrogen; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4--C₂ H₅ SO₂ --; R⁹ is ethyl; and R¹⁰ is ethyl.
 8. The compound of claim 2 wherein R is nitro; R¹ is hydrogen; R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4-trifluoromethyl; R⁹ is ethyl; and R¹⁰ is ethyl.
 9. The method of controlling undesirable vegetation comprising applying to the are where control is desired, an herbicidally effective amount of a compound having the formula ##STR23## wherein R is halogen, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, nitro; C₁ -C₂ haloalkyl, or R^(a) SO_(n) -- wherein n is 0 or 2 and R^(a) is C₁ -C₂ alkyl;R¹ is hydrogen or C₁ -C₄ alkyl; R² is hydrogen or C₁ -C₄ alkyl; R³ is hydrogen or C₁ -C₄ alkyl; R⁴ is hydrogen or C₁ -C₄ alkyl; R⁵ is hydrogen or C₁ -C₄ alkyl; R⁶ is hydrogen or C₁ -C₄ alkyl; R⁷ and R⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) nitro; (7) C₁ -C₄ haloalkyl; (8) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen; (c) phenyl; or (d) benzyl; or (9) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R⁹ is hydrogen or C₁ -C₄ alkyl, R¹⁰ is (a) hydrogen; (b) C₁ -C₆ alkyl, (c) C₄ -C₆ cycloalkyl, (d) halogen substituted C₁ -C₆ alkyl, (e) phenyl; (f) C₁ -C₆ alkoxy; (g) benzyl; (h) phenethyl; (i) C₂ -C₆ alkenyl; or (j) C₂ -C₆ alkynyl.
 10. The method of claim 9 wherein R is chlorine, bromine, C₁ C₂ alkyl, C₁ -C₂ alkoxy, nitro, C₁ -C₂ alkylthio or C₁ -C₂ alkylsulfonyl; R¹ is hydrogen or methyl; R² is hydrogen or methyl; R³ is hydrogen or methyl; R⁴ is hydrogen or methyl; R⁵ is hydrogen or methyl; R⁶ is hydrogen or methyl; R⁷ and R⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifloromethoxy; (6) nitro; (7) C₁ -C₄ haloalkyl; (8) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen; (c) phenyl; or (d) benzyl; or (9) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; and R⁹ is hydrogen or methyl and R¹⁰ is (a) hydrogen; (b) C₁ -C₂ alkyl; (c) cyclohexyl; (d) C₁ -C₄ alkoxy; (e) phenyl; (f) benzyl; (g) phenethyl; or (h) allyl.
 11. The method of claim 10 wherein R⁷ and R⁸ are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; nitro; trifluoromethyl; R^(b) SO_(n) -- wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; and R⁷ is in the 3-position.
 12. The method of claim 10 wherein R⁷ is hydrogen and R⁸ is hydrogen; chlorine; bromine; fluorine; trifluoromethyl; or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 13. the method of claim 10 wherein R is chlorine; R¹ is hydrogen; R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4-chlorine; R⁹ is methyl; and R¹⁰ is methoxy.
 14. The method of claim 10 wherein R is nitro; R¹ is hydrogen; R² is hydrogen; R³ is methyl; R⁴ is methyl; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4-chlorine; R⁹ is methyl; and R¹⁰ is methoxy.
 15. The method of claim 12 wherein R is methyl; R¹ is methyl; R² is methyl; R³ is hydrogen; R⁴ is hydrogen; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4--C₂ H₅ SO₂ --; R⁹ is ethyl; and R¹⁰ is ethyl.
 16. The method of claim 10 wherein R is nitro; R¹ is hydrogen; R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4-trifluoromethyl; R⁹ is ethyl; and R¹⁰ is ethyl.
 17. A herbicidal composition comprising a substituted 3-amino-2-benzoyl-cyclohex-2-enone compound of the formula ##STR24## wherein R is halogen, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, nitro; C₁ -C₂ haloalkyl, or R^(a) SO_(n) -- wherein n is 0 or 2 and R^(a) is C₁ -C₂ alkyl;R¹ is hydrogen or C₁ -C₄ alkyl; R² is hydrogen or C₁ -C₄ alkyl; R³ is hydrogen or C₁ -C₄ alkyl; R⁴ is hydrogen or C₁ -C₄ alkyl; R⁵ is hydrogen or C₁ -C₄ alkyl; R⁶ is hydrogen or C₁ -C₄ alkyl; R⁷ and R⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) nitro; (7) C₁ -C₄ haloalkyl; (8) R^(b) SO_(n) -- wherein n is the integer 0, 1 and 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen; (c) phenyl; or (d) benzyl; or (9) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R⁹ is hydrogen or C₁ -C₄ alkyl, R¹⁰ is (a) hydrogen; (b) C₁ -C₆ alkyl, (c) C₄ -C₆ cycloalkyl, (d) halogen substituted C₁ -C₆ alkyl, (e) phenyl; (f) C₁ -C₆ alkoxy; (g) benzyl; (h) phenethyl; (i) C₂ -C₆ alkenyl; or (j) C₂ -C₆ alkynyl and an inert carrier therefor.
 18. The composition of claim 17 wherein R is chlorine, bromine, C₁ C₂ alkyl, C₁ -C₂ alkoxy, nitro, C₁ -C₂ l alkylthio or C₁ -C₂ alkylsulfonyl; R¹ is hydrogen or methyl; R² is hydrogen or methyl; R³ is hydrogen or methyl; R⁴ is hydrogen or methyl; R⁵ is hydrogen or methyl; R⁶ is hydrogen or methyl; R⁷ and R⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifloromethoxy; (6) nitro; (7) C₁ -C₄ haloalkyl; (8) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen; (c) phenyl; or (d) benzyl; or (9) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; and R⁹ is hydrogen or methyl and R¹⁰ is (a) hydrogen; (b) C₁ -C₂ alkyl; (c) cyclohexyl; (d) C₁ -C₄ alkoxy; (e) phenyl; (f) benzyl; (g) phenethyl; or (h) allyl.
 19. The composition of of claim 17 wherein R⁷ and R⁸ are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; nitro; trifluoromethyl; R^(b) SO_(n) -- wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; and R⁷ is in the 3-position.
 20. The composition of claim 1 wherein R⁷ is hydrogen and R⁸ is hydrogen; chlorine; bromine; fluorine; trifluoromethyl; or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 21. The composition of claim 1 wherein R is chlorine; R¹ is hydrogen; R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4-chlorine; R⁹ is methyl; and R¹⁰ is methoxy.
 22. The composition of claim 17 wherein R is nitro; R¹ is hydrogen; R² is hydrogen; R³ is methyl; R⁴ is methyl; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4-chlorine; R⁹ is methyl; and R¹⁰ is methoxy.
 23. The composition of claim 17 wherein R is methyl; R¹ is methyl; R² is methyl; R³ is hydrogen; R⁴ is hydrogen; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4--C₂ H₅ SO₂ --; R⁹ is ethyl; and R¹⁰ is ethyl.
 24. The composition of claim 17 wherein R is nitro; R¹ is hydrogen; R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen; R⁵ is hydrogen; R⁶ is hydrogen; R⁷ is hydrogen; R⁸ is 4-trifluoromethyl; R⁹ is ethyl; and R¹⁰ is ethyl. 